Xanthinealkanoates of diarylmethoxy-



ate-i;

U d S nlt tatas lc Patented Mar. 8, 1955 methylaminoethyl benzhydryl ether melting at about 2,703,803 6l64 C. It has the structural formula XANTHINEALKANOATES OF DIARYLMETHOXY- CHr-III-C=O CHr-COOH N(CH|):

ALKYLDIALKYLAMINES 0:0 & ahoaroqsflwflmz Albert L. Raymond, Northfield, and John w. Cusic, I Skokle, 11]., assignors to G. D. Searle & (30., Chicago, "L, a corporation of Illinois No Drawing. Application May 31, 1952, Example 2 serial 29L: 30 parts of theophylline ti-acetic acid and 60 parts of 1 Claim. (Cl. 260-253) fl-dimethylaminoethyl benzhydryl ether are dissolved in tOO parts of butanone and ZO parts of water with heat- The present invention relates to methylated xanthinel5 8- Aflel' (1001,1118 lwqtedwnh ether alkanoates of (diarylmethoxyalkyl)dialkylamines. These whereupon an ineclllliflte fqrms which 15 separated compounds can be represented by the structural formula and dried- There IS 1111,18 Obtained the s-lheophylllllcacetate of fi-dimethylaminoethyl benzhydryl ether as a hygroscopic amorphous solid melting at about 65-70 J} A; C. It has the structural formula 0: -N o.m.o0on Nflmrer nlkyl):

CHr-NC=O o lk-0--CH(Ar)| E (loweralkyD- N c-cm-oooa morn):

CHr-N- -N Hs-CKrO-CH(COH:)2 wherem n is an integer smaller than 4, Alk is a lower alkylene radical containing more than one carbon atom, Example 3 R is either-hydrogen or a lower alkyl radical and Ar is a monocyclic aryl radical. 80 10 parts of 3-methylxanthine-8-propionic acid and 25 Among the radicals which Alk can represent are such parts of -diethylaminopropyl di-p-tolymethyl ether are saturated bivalent radicals as ethylene, propylene, bu dissolved in 200 parts of butanone and 10 parts of water tylene, amylene and hexylene, wherein the propylene, with heating. After cooling the solution is treated with butylene, amylene and hexylene groups can be of the ether whereupon an oily precipitate forms which is sepabranched or unbranched type, and polymethylenes such 36 rated and dried. The resulting salt is washed with cold as trimethylene and hexamethylene. Ar is a monoanhydrous isopropanol and redried. The 3-methylcyclic aryl derivative such as phenyl, tolyl, xylyl,-haloxanthine-8-propionate of 'y-diethylaminopropyl di-pphenyl, anis l and phenetyl. tolylmethyl ether thus obtained has the structural formula It is the o ject of this invention to provide drugs which shown below. The salt shows on analysis 12.4% nidepress the vestibular branch of the eighth cranlad nerve d0 trogen.

int-oat) O-UHs-OHr-OOOK mom, Ooh, OE:- N (smile-0W andwhichlackinterleringlidereaetiomsuchspe- Weclaimt ciflcdepressantsareot'valueindiseaseswith The salt ofthestructuralformula dycglsflfictionsfgf labyrinthine system. These are parom-N-0=o 0111-0001! Name: in y use l m e centre of WWI": nausea. o: Krom 0mmm Example 1 I OH f m h um 7 id and a partso eopy'e -aoetieac parts cu of fl-dimethylaminoethyl benmydryl ether are dissolved no in the me of m pawn in 200 parts of hot butanone, cooled and treated with Um MATES PAWS ether. The resulting oily precipitate is separated and 2,534,235 Cusie Dec. 14, 1950 vacuum dried to yield the 7-theophyllineaeetate of 5 2,595,853 Horeloil May 6, 1952 

